This invention relates to novel N-(heterocyclicaminocarbonyl)arylsulfonamides in which the aryl radical is substituted by two carboxyl radicals. The compounds of this invention and their agriculturally suitable salts, are useful as agricultural chemicals, e.g. plant growth regulants and herbicides.
Netherlands Patent No. 121,788, published Sept. 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl or 1-4 carbon atoms. PA1 R.sub.2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl. PA1 when Q is ##STR10## then R is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, and R and R.sub.1 can be taken together to form --(CH.sub.2).sub.4, --(CH.sub.2).sub.5 --, and --CH.sub.2 CH.sub.2 O--CH.sub.2 CH.sub.2 --; PA1 X is CH.sub.3, CH.sub.3 O, CH.sub.3 CH.sub.2 O or Cl; PA1 Y is CH.sub.3, CH.sub.3 O(CH.sub.2).sub.n' where n' is 0, 1 or 2, CH.sub.3 CH.sub.2 O, or R.sup.2 O.sub.2 CCHR.sup.1 O where R.sup.1 is H or CH.sub.3 and R.sup.2 is H or C.sub.1 -C.sub.3 alkyl; PA1 Z is CH, N, or C--CH.sub.3 ; PA1 with the proviso that when Q is ##STR11## then the floating ##STR12## must be in the 3 position. PA1 (1) those compounds of the generic scope in which W is O; PA1 (2) those compounds of Preferred 1 in which Q is oxygen; PA1 (3) those compounds of Preferred 2 in which Y is CH.sub.3 --, --OCH.sub.3 or ##STR13## and X is CH.sub.3, CH.sub.3 O or CH.sub.3 CH.sub.2 O; (4) those compounds of Preferred 3 in which R is CH.sub.3 or --CH.sub.2 CH.sub.3.
U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2## wherein R.sub.1 is hydrogen or lower saturated aliphatic acyl and
The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.
French Patent. No. 1,468,747 discloses the following para-substituted phenylsulfonamides as being useful as antidiabetic agents: ##STR3## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al. Chem. Ab., 53 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR4## wherein R is butyl, phenyl, or ##STR5## and R.sub.1 is hydrogen or methyl.
When tested for hydroglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR6## Based upon similarity to a known compound, the author speculated that the foregoing compound might have a hypoglycemic activity.
Substituted-pyrimidinyl sulfonylureas of the following formula, which are also para-substituted on the phenyl ring, are disclosed in Farmco Ed. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959)]; ##STR7## wherein R=H or CH.sub.3.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basid food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.